


Graduating Rory

by yorkshirerose18



Category: Gilmore Girls
Genre: F/M
Language: English
Status: Completed
Published: 2018-03-18
Updated: 2018-08-20
Packaged: 2019-04-05 02:03:28
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 8
Words: 13,630
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14033766
Author URL: https://archiveofourown.org/users/yorkshirerose18/pseuds/yorkshirerose18
Summary: Rory is finally graduating from Yale after a tough ride to get there.With support from her Mom, Luke and Jess, Rory finds herself starting the next chapter of her life.





	1. Let’s get you Graduated

**Author's Note:**

> Hey guys! This is my first posted AO3 fic, so please review and tell me what you think!
> 
> Set in AU Summer 2007.

“Rory! Time to get u-up!” Lorelai’s loud, sing-song voice echoed through the walls of her childhood home. It was finally here, graduation day. A rollercoaster it had been leading up to this moment. Between finding her now ex-boyfriend Logan Huntzberger in bed with her now ex-Chilton friend Louise right in the middle of her final year, as well as unexpectedly losing her Grandfather just months prior, she thought that this would all be an impossible dream. But with the support network around her, especially her strong matriarchal role models the Gilmore Girls Lorelai and Emily, not only did she very successfully co-edit the Yale Daily News with her best friend Paris, but also came out a stronger, more independent woman with a double major in English Literature and Journalism, not to mention she has also received a frenzy of job offers climbing out of the woodwork. 

“LORELAI LEIGH GILMORE GET YOUR SMART LITTLE BUTT OUT OF BED!” Rory stretched and yawned. She managed an inaudible noise in return, loud enough to inform her mom she was really awake and quickly checked her phone. After a few moments she got up and headed towards the Ensuite that Luke had recently installed. He had done this after she moved back home, with her not being able to face living on campus after the Logan scandal, he wanted to give her some space of her own. After a refreshing hot shower to start off her busy day ahead, she emerged into the bedroom in her dressing gown, sulking dramatically after spending 10 minutes in front of her closet failing to decide what to wear on such a momentous day. It was so unlike Rory Gilmore to be ill-prepared. 

“Why the long face hon?” Lorelai asked with concern whilst handing her a coffee mug which Rory graciously accepted.  
“I can’t decide what to wear” Rory whined after a few large mouthfuls of Luke’s coffee. “Its just that today is such a special day and I don’t want to get it wrong! I will be looking back through albums with my children and their children and I can’t have them thinking that their crazy mother couldn’t dress herself!” She rambled.  
“Aw jeez” Luke sighed as he put a plate of pancakes in front of her on the table, he busied himself back at the stove knowing full well it would be for the best to leave this one to Lorelai.  
“I knew this would happen and because I am the absolute brilliance that I am, I took it upon myself to get you an early graduation present” Lorelai said sheepishly, rewarding herself a very confused look from Rory as she turned to run upstairs. “Close your eyes!” she said when she reached the foot of the stairs. “No peeking!”  
“Mom I don’t have time to be doing this now, we leave in just over an hour’” Rory said hurriedly.  
“Luuuuuke, cover your daughter’s eyes please! I’m not coming into the kitchen until they’re closed! She’s got this reluctance from all these years of living with you!” earning a groan from both Rory and Luke.  
“Aw Jeez, Ror just do it to shut her up will you!” Luke said as he stood behind her and put his hand on her shoulder. “I’m sure you’re too old for me to be covering your eyes anyway” he added almost pleading with her.  
“Fine! Fine!” Rory admitted defeat and covered her eyes. She should’ve known that although it is her Graduation day, even Taylor Doose wouldn’t try and refuse Lorelai.  
“Okay.. open them..” Rory lowered her hands slowly. “Ta da!!” Lorelai beamed widely. Rory was in awe; she held a beautiful royal blue dress with spaghetti strap shoulders and a sweetheart neckline. It had a pleated skirt which would fall perfectly to just below her knee which was elegant and the perfect dress which she would ever dream of wearing today.  
“Oh mom, it’s beautiful! You didn’t have to get me anything, but thank you so much! I’m glad you were prepared!” Rory said gratefully whilst admiring her dress. Lorelai was clearly buzzing.  
“Sweetie, this is a Lorelai Danes spectacular made by yours truly, I knew you would need something to really remember this by and how everything has been lately, I knew you probably would forget that the dress is just as important as the diploma. Now finish those pancakes and get yourself ready! We have an hour until we have to meet Grandma in New Haven”. Rory scoffed down her breakfast and ran into her room to get ready, after giving her Mum a very grateful kiss on the cheek. 

She had allowed her hair to grow out to just above her breast and decided to have it half up and curled. She applied light make up and sprayed the perfume Luke had bought her for her 21st birthday onto her neck and wrists before finally slipping into the dress her mother made her. She was an image of absolute perfection, with her matching silver heels and clutch bag, she was ready to go. As she didn’t take too long, she had some time to spare. Turning to the machine, she refilled her coffee cup from earlier and whilst doing so was totally oblivious to the door opening behind her. 

“Wow Rory, you’re stunning” Jess smiled at her. She spun around fast to see him wearing a tailored dark grey suit with a black tie which she had assumed he had got for his book tour. She had to admit herself that he looked insanely handsome staring back at her, his messy hair had been styled and his five o clock shadow defined his jawline even more than usual. She threw her arms around him, she was so happy he could make it after she hadn’t seen him for months due to his book tour.  
“Not too bad yourself Mariano. I wasn’t sure if you were coming today, but I’m glad you’re here” she told him truthfully. With the recent release of his first novel, The Subsect, Jess was always busy now and wasn’t as easy to contact thanks to his press tours and book signings.  
“Of course I was coming today, no matter where Chris had planned me to be, I wouldn’t have been anywhere but here” he smiled softly at her as she stepped back to finish her coffee, prompting Jess to pour one for himself. “Besides, I’m taking all the credit for this diploma Gilmore, without me you’d be nothing” he smirked. Rory giggled after giving him a sarcastic look, even though it was technically true. It was Jess who convinced Rory not too give it all up after the Logan situation, not even her Mum, Luke or Paris were able to say what she needed to hear, but Jess knew exactly what to do when it came to Rory, he always did. Jess knew her better than anyone else. It took them having to go through that troubled time in their relationship to appreciate each other and build an unbreakable friendship based around a lot of love. They stood in comfortable silence for a moment finishing their coffees before Luke and Lorelai made their entrance to the kitchen. 

“Hey Jess, it’s good to see you! I’m glad you could make it today” Luke smiled and hugged his nephew. “Rory, you look lovely” he beamed at her, making Rory blush.  
“Thank you” she smiled and twirled to show Luke her dress. It had been 15 years ago when her mum finally started dating him and after they married 7 years later, although he never legally adopted her, she would always consider him to be her real father.  
“You’re both absolutely perfect!” Lorelai said whilst stepping forward and putting a hand on both of their shoulders, one hand had a camera swinging from the strap tied around her wrist. The foursome caught up on Jess’ daily life whilst finishing their coffees and Rory found herself smiling widely stood with the people who she loved dearly.   
“Let’s go then shall we?” Lorelai broke the comfortable silence. “Luke and I are picking Grandma up from Hartford on the way, so if you two wanna take Jess’ car we can meet you at the country club?” Lorelai suggested.  
“Sounds great” Jess smiled. “You don’t mind riding with me do you?” he looked to Rory.  
“Of course not” she smiled back. “Gives us chance to argue about books where the adults can’t moan at us” she quipped, giving them all a laugh.  
“Thank god!” Lorelai replied dramatically. “I understand that you are both absolute brainiacs with your published books and Yale diplomas, but I now know more about Hemingway and Austen than I do about the Kardashian’s and that is not okay!” She rambled whilst finishing Rory’s hair with final touches and a can of hairspray. One last look at her creation and she smiled softly. Jess was almost sure he had noticed her start to tear up slightly.   
“Come on Luke, let’s go. See you kids there” she dramatically blew them both kisses whilst backing up to the door. Luke followed behind shaking his head lightly, Rory waved and couldn’t help but chuckle slightly as she heard him call her a ‘crazy lady’ underneath his breath. Jess naturally took her mug and dumped them into the sink. He sat across from her at the table.  


“So how’ve you been Gilmore? You clearly look amazing so that puts me at ease” he smirked. Jess had worried about her a lot, she got herself into a really bad place a few months prior thanks to that blonde dick who he really, _really_ hated.   
“Shut up you” she swatted his hand and blushed deep crimson. “I’m actually doing really well. I’m deciding what job I want to take after today is done which has been stressful. I’ve got offers from New York, Hartford and Washington so far” she bit her lip.  
“Wow Ror, that’s incredible! Well done you” he took her arm again. “I’ve been offered two of them also” he caught her gaze.  
“WHAT? WHERE? DOING WHAT?” Rory excitedly fired questions at him.  
“Slow down hotshot” Jess chuckled whilst she blushed again whilst muttering an apology. “First one, they want me to open a franchise of Truncheon. Second one, I have choices, two of which are Hartford and New York. Third one, it’d be my branch. No Matt or Chris, just me and whoever I choose to work for me”.  
“Woah Jess, that’s absolutely incredible. Congratulations” she was stunned at this, but incredibly proud of him. “Yeah I am weighing up my options right now. If it helps, where I move to, I get my own place too. If you choose the same city, you can always live with me. It’d be a lot cheaper and hey, you’re decent company” he nudged her. “Just an idea though Ror, no pressure”.  
“Wow thanks, we can go through our options later on and see what we come up with”. She was clearly in deep thought.  
“Right, have you got everything you need miss Graduate?” This snapped Rory out of her daze as she headed to her room to grab a coat and her bag. He collected his keys, phone and wallet from the table.  
“Ready?” he motioned for her to lead the way as he unlocked his car. “Let’s get you graduated then” He smiled at her as the engine roared to life which she returned happily. Within minutes they were speeding off towards the country club, conversing about their usual literature banter just like old times.


	2. Lunch at the Club

**Summary for the Chapter:**

> The foursome meet Emily at the Golf Club for a pre-Graduation meal. Emotions run high as they all feel the absence of Richard Gilmore.

“Rory, my darling girl, congratulations on your success” Emily Gilmore said with such elegance and pride as she greeted her granddaughter inside the club. “You look simply lovely dear, as do you Jess, very good too see you, how’s the book tour going?” she embraced the pair and led the party to the function suite.  
“Great thanks Emily, I can’t wait for it to be over though, it’s been a long 3 months!” Emily beamed at him and replied something along the lines of how hard work will pay off in the end. Rory was not listening, instead took in her surroundings in absolute awe.  
“Wow Grandma, this room is beautiful” Rory complimented as she made her way around the room which had been decorated and made up for a banquet; it was very over the top, but very Emily Gilmore.  
“Yeah Mom, this must’ve been quite the effort for you, did you have any help?” Lorelai added.  
“Take a seat ladies” she motioned for them to join the men who were already seated at the grand dining table. “I actually did have some help”. She sighed sadly whilst sitting herself down at the head of the table, ushering the maid over to top up her glass.  
“Who do we owe our thanks too Mom?” asked Lorelai intriguingly.  
“Your father” she said very sadly, not missing the fact that each of the four were staring at her with very different emotions. “He set this whole thing up before he passed. In fact, he was so sure of Rory’s success, he started making arrangements the day she told us she had chosen Yale”. She smiled sadly, tears evidently starting to gather in her ducts. “Nobody would be more proud of you than he Rory” Emily’s voice broke. As much has this had warmed the hearts of everyone in the room, it had absolutely floored Rory, who immediately excused herself before running out the glass doors onto the course for some air. Lorelai was torn between following her daughter and comforting her mother, but Jess was immediately to his feet and following Rory out the door before she even came to her decision. Luke saw her guard go up at this and instinctively placed his hand on her lap, with a sure squeeze and an almost silent “let him handle it” she nodded knowing he was right and got up to comfort Emily. 

Meanwhile, Jess managed to catch up to Rory almost immediately guiding her to the nearby willow tree to stand under.  
“Hey, I thought you Gilmore’s didn’t run, especially in heels” he joked as he reached for her shoulders, managing to slow her to a complete stop. This earned him a half hearted punch on the arm, with a sobbing Rory collapsing straight into his chest. “Well I hope your make up is waterproof” he won a soft giggle from her which helped slow her cries.  
“It’s not fair Jess, he should be here!” She managed to sniffle out. “He believed in me so much and he never got too see me graduate!” She sobbed harder.  
“Ror, you know that’s not true. Of course he’s here, he’s right there” he pointed at her heart. “He had every right to believe in you, you’re the most intelligent, deserving, hard working woman I know. Hell, if you didn’t graduate the earth wouldn’t rotate anymore, we all knew you would do it. We have all along, because no matter what obstacles you’ve faced, you’re Rory freaking Gilmore! You overcame the bastards and prevailed stronger for it. He’s here today Ror, and he is so proud of you. We all are” he looked down at her small frame to see her still sobbing, but with a more somber expression. “What, Mariano pep talks not have the same effect on you anymore?” He smirked, causing her to crack.  
“Of course they do” she tearily smiled at him. “Did you really mean all that?” she steadied herself onto shaking legs and took full advantage of the extra height from her shoes to look him square in the eyes.  
“You have to ask?” He stared straight back into her baby blue eyes. “I’d never lie to you”. He almost whispered as he rested his forehead against hers. She impulsively leaned forward and kissed him, rather similar to how she had done at Sookie’s wedding 7 years ago. Without missing a beat, Jess put his arms around her and kissed her back with everything he had. He still loved her after all these years, of course he did. Through moving to Philadelphia straight after him finding out he hadn’t passed his senior year at Stars Hollow High. Through seeing her heart break as he watched her from afar during his many unnoticed visits back to the town after his failed reconciliation with his father in California. Through coming back again a published author, finding her with a douchebag with daddy’s trust fund who he knew wasn’t right for her. Through everything, Jess’s feelings for Rory had never once wavered, so for her to be kissing him right now, even if just out of the heat of the moment, for him to just taste her lips one last time, it was enough. Enough so that he could allow himself to have his heart broken all over again. 

When Rory finally pulled away, he kept his arms around her firmly, not yet ready to open his eyes to break the moment. He was expecting her to tell him it was just a mistake and that she doesn’t want to hurt him and didn’t mean to lead him on and blah blah blah. He certainly wasn’t expecting her response.  
“That part always worked didn’t it?” She sighed almost happily. “Come on, let’s go back inside before they send a search party hmm?”. He slowly opened his eyes and led her back towards the suite, as he reached for the door, she placed a hand on his arm causing him to freeze suddenly. “Thank you again for everything. You’re a great guy Jess Mariano”. He squeezed her shoulder in acknowledgment and smiled before opening the door for her to step in first. 

He let out the breath he didn’t know he was holding and quickly composed himself before following her back to the table. While the Gilmore Girls had turned their attention straight to Rory, Luke threw him a questionable look which he nodded in response. Luke’s understanding that everything was okay allowed his mind to wander back to what just happened. Jess knew this was going to be the longest day of his life but, he’d waited nearly 10 years for Rory Gilmore, another 10 hours couldn’t hurt, could it?

**Notes for the Chapter:**

> Hope you guys enjoyed the chapter, please review and let me know what you think!


	3. Caps, Coffee and CDs

**Summary for the Chapter:**

> Graduation over, Jess and Rory get a little bit more time together before the celebratory family meal.

After a final goodbye tour of Yale and the most emotional ceremony for the Gilmore Girls, Rory was finally graduated. The foursome had planned on returning to Luke’s so he could make them all a celebratory home-cooked dinner before the not-so ‘surprise’ party that Lorelai and Lane had planned at Miss Patty’s that evening. Emily Gilmore said her goodbyes in the halls after bumping into a few of Richard’s alumni friends that Rory would never remember the names of. She couldn’t help but notice a twinkle in Emily’s eye whenever she spoke about him and hoped that one day she could be that in love with a person, even after the ‘til death do us part’ vow. 

This brought her mind back to the events at the club earlier that morning. _What was she thinking just kissing Jess like that?_ After everything they had been through, him leaving, him returning with the confession of love just to leave again, him returning again to find her and Logan happy together, her to kiss him and lead him on with no acknowledgment for his feelings, the list could go on and on down memory lane. Either way, It was pretty clear that they just didn’t work and had a well known history of treating each another like shit. 

_But that was silly teenage recklessness_ , Rory reasoned with herself, she was 22 now and an Ivy League graduate - she could do anything! Besides, they had always worked those two hadn’t they? He was always the boyfriend she would go back to. He was the only person who didn’t see her as perfect little miss Rory, but as just Rory. He was the only person that could be so different yet be so similar and he never bored her, not once. Rory smiled to herself, realising not only had she mentally created a pro/con list for dating Jess again, but that she still loved him for all his traits and flaws. _Her_ Hoodlum, _Her_ Dodger, _Her_ Jess. 

“One more picture?” Lorelai walked over to her snapping her out of her thoughts and she smiled as her mom took a selfie. “You look as cute as a puppy dog.. aha!! That’s going in a frame. Cute little doggy finally got her bone!” Rory smiled and mock rolled her eyes at her mothers terrible humour.  
“That was a very difficult bone to achieve and I put in a lot of hard work and effort to get it thank you” she replied proudly.  
“Do I want to know what bone you put hard work into getting?” Jess smirked at her and cocked an eyebrow suggestively at her causing Rory to flush a dark shade of crimson  
“Dirty!” Lorelai giggled causing Luke to sigh.  
“Come on, we need to get back to prepare for tonight. Jess, you okay taking Rory back?”  
“Sure, definitely beats a lonely journey” he smiled at her. “Plus I don’t mind waiting for her to return the ol’cap and gown”.  
“You’re the best! Come on Luke, see you guys at home” Lorelai intended on sounding grateful but it came across more impatient.  
“Told ya those shoes weren’t gonna be comfortable enough!” Rory quipped as the older couple headed off earning a wave from her Mom. Then there were two.  
“So... lets join that queue and return those robes eh Hermione?” said Jess.  
“Sounds like a great idea Harry” Rory played along.  
“Ah, not Ron then? Always the best friend, never the lover” he playfully gave her a lopsided grin that just made her melt inside.  
“Now come on Mariano, you know full well that it was Harry who was destined to be with Hermione. JK Rowling herself even knows this, they were just so much better for each other and they were always th-”  
“Destined to be together huh?” Jess interrupted and Rory realised what she had said out loud.  
“Well Ron was an idiot” she tried to cool it out.  
“Whatever you say Gilmore” he dropped it to her appreciation though it was a topic of conversation that would be brought up soon enough. The pair stood in a comfortable silence whilst waiting for the line to shorten, Jess noticed Rory stifle a yawn into her gown and chuckled softly. “How about a trip to the coffee cart before we head back? For old times sake and so I don’t have to carry your sleepy butt to the car lot” she smiled. No matter what she tried to hide from him he always caught it.  
“That’d be nice thank you” she smiled up at him “you’re buying” she added cheekily with a wink.  
“Yes ma’am, I know better than to argue with a Gilmore about coffee when they’re without coffee” he said whilst putting an arm lazily around her shoulder. She instinctively allowed her head to drop onto his shoulder and swung her free arm back around his waist. It was so unlike Jess to show a public display of any kind of affection, but Rory was far too caught up in the moment to tease him about it. Before they knew it, they had finally returned the gown, bought two XL coffees and were en route back to Stars Hollow. 

Rory was messing around organising his CD collection. Although he had a top of the range car which meant Jess was playing ‘I fought the Law’ through his phone, doing this reminded her of being 16 again, in his beat up old car listening to the crackly second hand stereo. She reminisced the happy memories and allowed her mind to relive them, Jess caught her goofy expression out of his peripheral vision.  
“Well I’m pretty damn sure that The Clash isn’t putting that smile on your face Ror” this brought her back to reality, but her smile stayed nonetheless.  
“Just thinking is all, these CDs hold so many memories for me and it’s good to see them in good condition considering everything they went through” She paused. “Reminds me of us”.  
“Huh”. He replied, she could see he was in deep thought himself so didn’t push to talk about anything. She nervously shuffled the CDs in her hands waiting for him to say something.  
“I like the representation”. She looked at him quizzically as if asking him to explain further. “They’ve been through everything, seen some damage, followed me to New York and Philly, come back to Connecticut and even now, they still work perfectly”. She was unsure whether he was talking about them or the discs at this point.  
“Wow, when you put it like that I guess it’s a fairly good reminder” she agreed. The rest of the journey had been fairly quiet with the exceptions of Rory signing along here and there. Jess would drum his fingers against the steering wheel to the beat and occasionally nod his head along with her, she was very contagious. 

Before they knew it, they had arrived at the diner where balloons and a ‘Congrats Rory!’ banner were taped to the door. She smiled the widest grin and took a photo of it, before instructing Jess to take a picture of her in front of the door. As she went to take her phone back, she held onto his arm and whispered in his ear.  
_“We need to talk later”_  
She snuck under his arm into the diner leaving him alone to his thoughts whilst she rushed inside to be greeted by her mom with a glass of wine. Jess took a deep breath to compose himself, ‘damnit Mariano’ he cursed himself before pulling the handle and heading into the diner. 

“How was the drive back?” Luke questioned him. “We’ve been home an hour or so!”  
“Huh, you can thank the strict gown returns policy at Yale” he smirked in return.  
“Well rather you than us eh Lukey?” Lorelai interrupted. “Now where’s my dinner, diner boy?” She looked at him playfully which rewarded her with a head shake and a ‘crazy lady’ comment under his breath. She got up and gave him a big kiss on his shoulder and wrapped her hands around his waist whilst following him back into the kitchen, Rory smiled happily at them whilst Jess scrunched his nose.  
“What’s that look for?” Rory asked him.  
“What look?” He looked at her playfully.  
“This one” she mocked his earlier expression causing Jess to laugh at her. “Because if it’s Mom kissing Luke that made that face, I’d hate to think what you’ll be pulling later” she smirked.  
“Huh, why’s that Ror?” He smiled and leaned over the counter to get closer to her and he noticed her blush.  
“You’ll just have to wait and see”. She said confidently before jumping down from the stool and following her Mum to help in the kitchen. _‘Yeah’_ he thought, _‘we will’._


	4. Perfect

**Summary for the Chapter:**

> Rory’s night is ending, but is she ready to end the night?

It had turned out to be one of the most perfect evenings in Rory’s eyes. It seemed as though everyone in the town had brought her presents, which were kept stored, and unwrapped, in the back of Luke’s truck. They were to be opened the next day, allowing her to celebrate her whole educational career, starting from Day 1 all the way back to Stars Hollow Elementary. The guests all shared stories from the past, Rory found herself clutching her sides listening to Babette’s recollection of Rory’s first day and blushed a deep scarlet when Miss Patty gushed about her growing into the beautiful, intelligent young woman she is today. She had been mingling around all night, from person to person who all insisted on filling her cup full of more ‘punch’. 

She had been watching him all night from afar, drunk on both alcohol and her ludicrous thoughts, allowing herself to notice the tiny intricate details which drove her crazier about him. Like how he had been laughing and joking with Lorelai, which compared to their previous fighting 7 years ago was like watching two completely different people. It was rare seeing his chocolate eyes twinkle when he laughed, which made it all the more special. His mouth would fall open and his genuine smile showed which she loved. She loved how he and Luke would busy themselves by working in perfect unspoken synchronisation at the diner, as if he was back being the angsty 17-year old kid from New York she started falling for again. At the party, she watched him catch up with Lane about music and tours, and when they were interrupted by her twin boys pestering him for his attention, he humoured them with high fives and childish conversation, similar to how he acted with Zach whom he couldn’t stand to be around for longer than 5 minutes at a time, something to do with his ‘moronic idiosyncracies’ as Jess described them. 

Her favourite detail that she had observed about him was how great he looked in that suit, it was something she had familiarised herself with since her morning coffee. Rory found that she could not wait to end the night so she could repeat her earlier performance, which was probably spurred on by the copious amount of punch she had totalled throughout the evening giving her some Dutch courage. Luckily, the last few people were gathering their things to leave and started making their way out of the studio.  
“I know it’s your party and all kid, but I really need to get your mother home” Luke said as he was sat with a drunkenly sleeping Lorelai on his knee. Rory, though tipsy herself, saw the perfect opportunity to capture that moment as possible leverage in the future. Lorelai had peaked rather early on into the party, which was great to watch, but not so great when the stories were being told. She didn’t mind, her mom always supported her through everything and today had been just as much her celebration as it had been Rory’s.  
“You need help?” Jess came over after seeing the final guests out. “I know better than to wake a sleeping Gilmore” he smirked and Rory blushed.  
“Nah I’m good, my trucks just outside. I knew it’d be a good idea bringing it over, she’s been like the Duracell bunny since she woke up so alcohol or not, I knew this would happen”. He stood with her in his arms and it looked effortless. ‘We can open your gifts tomorrow when she is sober enough to appreciate them’ he added, nodding a parting goodbye as he passed them and took off down the steps.  
“So..” Jess got her attention as they both busied themselves finishing clearing the mess. “Have you enjoyed it?”  
“Its been a very special day” Rory smiled at him, tying the last bin bag of plastic cups, which he took off her to throw in the trash.  
“How about some coffee? I have some clothes in the apartment you can borrow, which saves you having to walk all the way home”. Rory flushed at the thoughts going through her mind. “Plus, it’s as good a time as any to have that talk you wanted”. She caught his gaze and smiled.  
“Okay, let me just get these devil shoes back on” she looked physically pained at the sight of them and started mentally preparing herself for putting them back on.  
“C’mere” Jess instructed her to jump on his back. “You clearly don’t want them on, plus you weigh less than the textbooks I’ve carried for you, so jump on”. She giggled and immediately put her arms around his shoulders and got up to a comfortable position where she could fully appreciate his muscular body underneath her. This made Rory’s thoughts go into overdrive.  
“Is there still coffee in the apartment?” She asked him as he carried her over to the diner.  
“Yeah, why would you like to get me upstairs Miss Gilmore?” He said suggestively, here came the liquid confidence.  
“With how your ass looks in them pants Mr Mariano, I’m dead set on getting you upstairs”. Jess smirked and put her down so he could reach up to grab the spare key and open the diner. Once they were inside and had locked back up, they were hungrily kissing each other up against the door, as if they would die from deprivation. Jess spun them around and expertly manoeuvred around the tables towards the stairs. He picked her up and she responded by wrapping her legs tightly around his waist without breaking the kiss once. She found her hands buried into his hair, gripping at the back of his neck with every step he took until he finally got them to their desired destination. He gently placed Rory down on the spare bed and hesitated as Rory hungrily reached up to be reunited with his lips. 

“Wait” Jess stopped them. “What about that talk?” Rory sighed and pulled him down on to her.  
“I feel like there isn’t much that needs saying right now” she started kissing his neck and he groaned in frustration when she stopped suddenly. “Unless you don’t want this” she froze and turned her face away.  
“What could possibly make you think that I don’t want this?” He gently pulled her chin so he could look her in the eyes. “Maybe this isn’t the best time to say this but you’re exactly what I want, you always have been and you know we were meant to be together. It’s just, you’re drunk and I don’t want that to be the only reason this is happening”. They moved to be sat upright facing each other on the bed.  
“You think you mean that little to me that I’d make this a drunken one-night stand Jess?” She looked him dead in the eyes. “Yes okay, I’m a little wavy, but that doesn’t make what we’re doing here any less real. You know my feelings for you Jess” she said softly.  
“Do I though?” Rorys expression turned serious and defensive as she allowed him to continue. “We’ve spent years dancing around each other, I’ve watched you with other guys, we’ve been cities apart and not one damn day has gone by that you’re not part of mine. Rory, you’re it for me okay? I love you and I never stopped” Jess looked away, scared of rejection, feeling vulnerable to have just spilled all his deepest thoughts to the woman he loved. Rory let out a sigh.  
“Jess, of course I love you. The day you left for California broke my heart! I wasn’t ready to give up on something that you was - let me finish!” She hushed him with a finger to his lips. “-and I was absolutely crazy about you. After the party where it all went wrong, I got home that night and thought about what could’ve happened if I hadn’t have stopped you. I wish I never did, I really wanted you to be my first. But I did, so I have to live with that and I will never forget that damn bus ride to Chilton, god how stupid of me to not notice you had all your stuff under the chair!”  
“Rory!” Jess said loud enough to end her ranting. She paused and slowly looked up to meet his gaze.  
“Yes I loved Logan, but it was nothing in comparison to what we had and what I felt, feel. What I’m trying to say is that I want to be all in too and that you’re also it for me. I knew it from the moment you told me you don’t read much before attempting to steal your uncles beer from our fridge”. Jess was visibly beaming.  
“So, where does this lead us?” He asked.  
“Well” she said seductively whilst wrapping her arms around his neck. “Let’s start with something we always know works best”. He leaned in to meet her kiss, both smiling against each other’s lips in pure bliss. This had by far been one of the best days of Rory’s life.


	5. Pros, Cons and Pancakes

**Summary for the Chapter:**

> Now she had Graduated, the future awaits Rory Gilmore.

Rory awoke to the unfamiliar feeling of warm breath tickling her neck and found herself firmly wedged in between a muscular arm and a mattress. She smiled to herself as the previous night slowly replayed itself in her mind and happily leaned fully back into him pressing her spine against his chest, losing any possible distance between them. She was rewarded with gentle, sleepy kisses from Jess trailing from her neck round to her collar bone.   
“Good morning to you too beautiful. What an excellent way to wake up” he hummed against her skin.   
“I agree, although maybe without the headache next time” she turned her neck to face him.   
“Next time?” Jess smirked at her instant blush. “I’m kidding, of course there’s going to be a next time Ror. I told you, I’m all in” the pair shared a smile and a kiss.  
“What time is it?” She asked whilst yawning.   
“07:30” Jess replied.   
“Ugh we’d better get up and head to the shack before they come over here and find us” Rory moaned whilst getting herself up and headed over to the bathroom. Jess tiredly rubbed his eyes before hastily following her to also get ready for the day. 

“MOM? LUKE? BREAKFAST!” Rory shouted into the house with Jess following suit holding food and coffee from the diner.   
“Bless you child!” Lorelai replied from upstairs. The pair went to set the table up whilst the older couple shuffled around to ready themselves to join them.   
“Morning guys!” Luke smiled at the pair thankfully “it’s nice to be brought food for a change” he quipped receiving a stuck out tongue from Lorelai as she made her way round the table with hugs.   
“Don’t get used too it Uncle Luke” Jess smirked “I’ll be setting off for New York tomorrow morning”   
“For how long?” Rory asked quickly causing an eyebrow raise from Lorelai.   
“Two more weeks as I have 9 stores to visit and then I have roughly 5 weeks left in Philly, depending on how fast it takes to build a book shop”  
“Why are you building a bookstore Jess?” Luke asked clearly intrigued.   
“Truncheon wants me to open a new branch in one of five places. I think they’re heading for New York but ultimately it’s my decision” he shrugged.   
“Rory might also be moving to New York isn’t that right hon?” Lorelai added with her own smirk.   
“Yeah maybe” Rory continued to eat her pancakes.   
“We spoke about this already. I offered her a place to stay until she finds her feet if we do end up in the same city. Truncheon will provide accommodation for me, all I pay is bills. It is very beneficial and it makes a lot of sense”  
“Jeez, that’s awfully kind of you” Luke said with a confused expression.   
“Yeah, it’s nothing. She’s actually really tidy and I could use the friendly face” he smiled at her.   
“It’s always handy to know you’re both looking after each other when you’re there if that does happen” Luke added.   
“It probably will on my end” Rory added, receiving a confused look from Jess.   
“What do you mean?” He questioned her  
“Yeah hon. You’ve been awfully quiet this morning” Lorelai looked concerned   
“I got an email yesterday morning” she didn’t once look up from the coffee cup in her hands. “I didn’t say anything as it was graduation but now seems to be the perfect way to tell you all. I officially have an interview for the Times next week!” She smiled widely and allowed herself to look up. She found a beaming with pride Luke, Lorelai nearly choked on her food with happiness and Jess grinned enthusiastically.   
“Look, I don’t wanna get your hopes up. I mean, it’s only an interview....” Rory said.   
“Yeah well, its an interview for the New York Times!” Lorelai reached over to touch her arm supportingly. “Your dream may be a reality very soon and you’ve literally just graduated!”  
“I know!” Rory smiled widely.   
“Thats amazing Ror, you’re gonna blow them away!” Jess supported her. “When’s the interview anyway? If it’s in the next two weeks, I can and will be there”.   
“That’s the thing”. Rory said nervously. “The interview is two days from now. I’ll need to prepare and accommodate and did I mention I need to prepare?!” She rambled.   
“Woah slow down babe” Lorelai said firmly. “The moment we are done with breakfast we will start preparations! I can play hooky at the inn for this”   
“I can’t play hooky kid” Luke said. “Lane’s got the twins at the doctor so I already said I would cover her” he looked guilty.   
“Oh, that’s okay Luke, I have mom and Jess” she told him reassuringly.  
“Lorelai if you need to be at the inn, I’ll happily hold the fort here. I’ve seen thousands of her pro/cons lists and apparently I’m quite the expert with my Mariano pep talks” Jess offered with a smile.   
“Well Michel could handle it, but threes a crowd right?” she smiled at the pair. “Just let me know if there is absolutely anything I can do to help okay hon?”  
“Same here” Luke added.   
“Course, thank you both” Rory enthusiastically replied. They continued the remainder of their breakfast in comfortable silence.   
“Right well I better head to the diner” Luke stood to acknowledge his departure.   
“Shoot, I left my coat there last night! I’ll hitch a ride with you and walk onto the diner. Looks to be a beautiful day anyway”  
“Ok you ready?” Luke asked.   
“Yeah, bye kids!” She yelled whilst closing the door. 

Rory and Jess started to clear away the mess from the meal, they allocated themselves a job to do and she turned from him to start washing the dishes. Jess collected and cleared the table of containers easily so reached over Rory for a tea towel to help her, managing to get close enough to cause her to shiver which flustered her. Jess took his time in moving to prolong the reaction he’d caused  
“You wash, I’ll dry” he whispered into her ear.   
“S-sure” Rory stuttered out whilst focusing on scrubbing the same plate over and over.   
“I think that’s clean now Rory” he laughed.   
“Oh, right sorry” she said embarrassed and handed him the plate. She forgot to drain the remaining water from the plate and it soaked Jess right down the front of his shirt.   
“Crap!” Rory yelled whilst Jess was howling with laughter. “I’m so sorry Jess!” She said whilst taking the tea towel from his hands and attempted to dry him off with it.   
“Rory stop” Jess finally managed to speak. “As much as I appreciate you’re sorry, I’m afraid you’re making it worse”. She stepped away and they locked eyes. The twinkle in Jess’ brown orbs was enough to break Rory out of her awkwardness and she too started laughing along with Jess.   
“Oh, you think this is funny huh Gilmore?” Jess smirked.   
“Well, it’s a little funny” she retorted. Jess smiled at her with a glint in his eye.   
“Well, I don’t want to get ill so I should get out of my wet clothes, don’t you think?”   
“Um, yeah it’s probably a good idea” Rory said with a blush. Jess proceeded to slowly remove his shirt revealing his toned abs to her and she found herself unable to avert her eyes.   
“Like what you see huh?” Jess smirked causing Rory to turn a deeper shade of red.   
“Um, y-yeah” she stuttered shyly.   
“Well” Jess said seductively whilst stepping closer to her. “I like what I see too” he looked her up and down.   
“Jess I-“ Rory started as she also stepped into his embrace. This kiss was very similar to the one outside the Club yesterday, but was filled with much more passion. They quickly found themselves in Rory’s bedroom and her shirt had been discarded onto the kitchen table along with Jess’s. 

The pair finally managed to make it back into the kitchen fully dressed and in work mode. They had gone over Rory’s materials, interview techniques and four pro/con lists until her stomach started growling.   
“I think someone’s worked up an appetite” Jess said whilst leaning over to close her laptop screen.   
“Hey! I was busy!” Rory protested and tried to reopen her laptop without success.   
“You will be fine. We’ve been at this for two hours now, we need to eat. You’re a Gilmore, you definitely should not be fighting me about the offer of food!” Jess crossed his arms and pulled his ‘I’m right, you’re wrong’ face.   
“Well I guess you’re right...” she conceded.   
“C’mon, grab your coat let’s go to Luke’s” Jess instructed, to which Rory obliged and waited for him by the door, a very distracted look crept upon her face. He noticed this and put his arms around her waist, kissed her on the forehead and pulled her into an embrace.   
“You really shouldn’t worry Ror” he reassured her.   
“It’s my dream Jess, I can’t screw it up” she bowed her head and knitted her eyebrows together sadly.   
“Hey, look at me” He lifted her chin until eye contact was made. “You are going to be just fine. You were the editor of an Ivy League college’s newspaper, you’ve had enough experience and glowing references. Also, you have networked and you are an amazing writer. You put me to shame and some idiot published me!” Rory smiled at that.   
“Yeah, I guess you’re right. Thank you Jess” she leaned forward to kiss him again. “Can I ask you something?” She hesitatingly asked.   
“Anything” he replied without missing a beat.   
“When this interview is over and my head is not a mess anymore, can we figure out us?” She nervously averted her gaze.   
“There’s nothing to figure out Rory, I love you. We’ll take it however you want it, I’m ready” they regained eye contact and that alone told her everything she needed to know. His beautiful chocolate eyes stared into her soul and showed so much love and that alone convinced Rory that everything would be okay.   
“I love you too Jess... But I don’t think we should go public until Mom and Luke know about us though”   
“Smart, can’t have Lorelai hating me again. It’s taken me years to form this bond” he joked and caught her smiling lips with his once more.   
They passionately kissed in the doorway for a while until they were rudely interrupted by Rory’s stomach. The pair shared a laugh.   
“Come on Gilmore, you’re gonna waste away on me!” He let go of the embrace to push her out the door and led her over to Luke’s.


	6. Somewhere in Hartford

One exhausting, unnecessarily long, unbearable week. That’s how long it had been since the interview for her dream job. In those 7 gruelling days, Rory had been patient. She had kept her phone fully charged and on the highest volume, making sure she tucked it safely into whichever pocket she deemed most convenient of each outfit. It was by her side night and day and now, she was going out of her mind with stress. She and Jess had decided to take things slow the minute she stepped out of the Times building to him waiting for her with coffee ready. It was still a secret as they had decided to tell Luke and Lorelai together, which they wouldn’t have the opportunity to do for a few more weeks with Jess’ book tour still ongoing. She was thinking about the hours they’d spent after her interview hanging out in New York and started thinking about their future together, she was in such a daydream she was oblivious to the sound of the front door. 

“Rory? Hello?!” She heard a familiar shout from the hallway which immediately distracted her from her thoughts.   
“Paris? What are you doing here?” Rory said surprised, yet still smiled and embraced her warmly.   
“I received a phone call from a very, very worried person, who you never told me was around again by the way! I wasn’t expecting to hear from Rory Gilmore’s high school boyfriend!” She crossed her arms.   
“Wait Jess asked you to come around? Why? Also, how did Jess know to contact you?” Rory asked confused. “And why is he concerned?”   
“Beats me” Paris said sarcastically. “Okay twenty questions, first things first, let’s get you a coffee and I can fill you in on why I’m here. The condition is that you tell me everything that I’ve missed in the 12 days since graduation!” She took Rory’s arm and lead her to the door.   
“Yes sir” Rory sarcastically rolled her eyes and mock-saluted her, following her to Luke’s. 

“Hey guys!” Lane greeted the girls with a smile and a hug. “I’ll bring coffee and take 5!”   
“Great, I need you for back up!” Paris said.   
“Uh Oh, that’s not good. Hold on, CEASER I’M TAKING FIVE!” She yelled and sat with them.   
“So, when does my interrogation start?” Rory sighed.   
“When were you gonna tell me you got back with James Dean, Gilmore? I should’ve known, you were all heart eyed and PDA at the graduation” Paris looked her straight in the eye.  
“Wait, What?!” Lane exclaimed with surprise.   
“I’m not back with him! We’re just friends for now” Rory reassured herself more than the girls. “And we were not heart eyes and PDA!” She quickly added  
“Sure.. so does he know that you’re not back together huh?” Paris questioned. “Do YOU know that yourself?” She added. Rory sighed and put her head in her hands.   
“Ughhhh fine! I really don’t know, we talked and decided it might be time to start things over. I think I still love him after all this time” the girls stared at her in shock “After everything we’ve been through these past few years, he’s the one guy I can always count on. He’s been making that very clear since that night he came to our dorm. But for now, he’s publicising his book and I have a string of interviews for jobs” she started.   
“Yeah but if you get this job, you’ll both be in New York. You will be in the same place at the same time, you’ve not had that since high school” Lane said. “Plus, I’ve always known you still loved him, you never got closure!”  
“I know you’re right. I mean, he even offered me a place to live if we both end up in New York for good! That means something serious for me, right?” Rory sighed.   
“Damn it Gilmore, this could be your opportunity to settle. Yeah, you’re 22, but look at us. Lane has Zach and the twins and I’m walking down the aisle next month. You could finally have what you deserve, especially after Logan” Paris lectured.   
“Yeah I guess. None of this matters if I don’t get this Times job though. Not only is this my dream, but it could potentially be my whole life plan!” Rory was starting to get herself upset until her phone rang. “Oh my God, it’s the Times!” She freaked out.   
“What are you waiting for? Answer it!” Lane excitedly said. Rory took a deep breath and pressed the green button.   
“Hello, Rory Gilmore speaking” She said as confidently as she could through the nerves. Paris and Lane were staring at her so intently they could’ve burned a hole through her skull. Both of them tried so hard to analyse her expressions and replies to try and work out what was happening in the conversation, that was until..  
“OH MY GOD THANK YOU! YES, I CANT BELIEVE IT, THANK YOU! SEE YOU IN TWO WEEKS, THANKS AGAIN!” *click*  
“OH MY GOD I GOT THE JOB!” Rory squealed as the three girls embraced into a giant hug and found themselves bouncing around the diner. Luke came barrelling from the kitchen when he heard the disturbance.   
“Rory what on earth is going on?” He asked worriedly.   
“I got it!” She managed to say as Luke threw his arms around her with pride.   
“That’s fantastic news! We must celebrate! Phone your mother and tell her to meet us at home! DINERS CLOSED PEOPLE, TAKE WHAT YOU GOT AND LEAVE! ITS ON THE HOUSE!” He shouted with the biggest smile on his face whilst shooing out the remaining diners. Rory rang the inn immediately and waited rather impatiently for Lorelai to answer.   
“Dragonfly Inn, Lorelai sp-“  
“MOM I GOT THE TIMES JOB!” Rory shouted down the phone.   
“AHHHHH! OH MY GOD! THATS FANTASTIC NEWS HONEY CONGRATULATIONS!”   
“Thanks Mom. Luke says you need to meet us at home ASAP and we’re going out to celebrate”   
“Yes Miss New York! Ahhhh I can’t wait to see you! I’m so happy for you, see you soon, I love you!” Before Rory could reply the phone went dead and Luke was ushering the three out the door to the shack. 

Rory found herself staring at her phone on the ride to the house in the back of Luke’s truck.   
“Ring him then!” Lane instructed her.   
“But maybe he’s busy..” she started.   
“Rory, either you ring him or I’ll get Paris to do it!” She threatened. Poor Luke was dealing with Paris sat in the front, she had her Dior pantsuit on and could not get into the back of the ‘filthy truck’.   
“Okay, okay! I’m ringing him!” Rory sighed in defeat and dialled Jess’s number.   
After a few rings he finally answered.   
“Hey you!” Jess answered cheerily.   
“Hey.. so I have a question to ask you” Rory said.   
“Okay shoot” Jess replied.   
“Is the offer of roommate in New York still available?” She asked shyly.   
“You got the Times job?” He said excitedly.   
“Yes, I found out ten minutes ago! I start in 2 weeks!” She replied with the same excited tone.   
“That’s incredible, congratulations Ror! I told you that you’d blow them away! I knew you could do it! Of course the option is available. Quite good timing actually, I’ve signed the contract for it yesterday, I move in next week!” He said excitedly.   
“Wait, I thought you’d be in Truncheon for another 5 weeks?” She questioned.   
“Yeah, me too. Turns out the decision wasn’t all mine and they built the store whilst I was on this tour. I must say, although I’m slightly pissed that I had no input in it, it is rather convenient” he chuckled.   
“Wow, I guess so” Rory agreed.   
“So, how are you celebrating?” Jess questioned.   
“Luke insisted in closing the diner and Mom is leaving the inn early. We’ll probably just go to dinner in Hartford somewhere, Lane and Paris are with us too” she told him.   
“Hartford huh?” Jess said vaguely.   
“Yeah... why?” Rory intriguingly asked.   
“I’m in Hartford right now and I’m all done for the day. I can meet you guys somewhere if you don’t mind the tag along?” He suggested.   
“Of course! I’d love nothing more” she eagerly replied.   
“Great, text me when you have a plan. Anyway, I better run so congratulations again! See you tonight” Jess said happily.   
“Yes you will” she hung up the phone and smiled to herself.   
“Rory Gilmore you are smitten!” Lane teased.   
“Oh be quiet!” She replied, thankful for the timing of the truck pulling into the drive. 

An hour later, Lane had to get back to the twins and Paris had to get ‘Harvard routine ready’, so the trio all got their glad-rags on and hopped into Rory’s ‘least dirty’ Prius and headed for Hartford. They had planned to go to an Italian restaurant which was conveniently three blocks away from the hotel Jess was residing in, which got him there slightly early. Luke was the designated driver so went to park the car with Lorelai, whilst Rory got out to greet him by the door.   
“Congratulations!” He said with a smile as he greeted her with a quick kiss and lifted her into his arms and twirled her around in celebration.   
“Thanks! I’m so happy I could burst!” She replied when he finally put her down.   
“I wouldn’t recommend that” he joked with her and she giggled.   
“Rory Gilmore, did you just giggle?” Lorelai mocked in fake shock which earned a smirk from Jess.   
“What no!” Rory said defensively causing the two to laugh out loud.   
“Hey you two! It’s Rory’s celebration night, you can tease her tomorrow!” Luke scolded.   
“Yeah! Come on, let’s go eat I’m starving!” Rory added, leading everyone inside. They were greeted by a very cheery waitress and led to their table with complimentary wine. Rory sat next to Jess and was opposite her Mom, Lorelai was sneakily glancing at the pair and it was a mirror image of looking back at the two 5 years ago. They were smitten with one another, or at least trying not to be, but if anyone could read Rory as well as she had read the Gilmore library, it was her mom. 

“I’m thinking I would like bruschetta to start with” Rory said absentmindedly.   
“I’m thinking I need to go to the little girls room, join me?” Lorelai said with a hint of urgency.   
“But we haven’t ordered yet?” Rory questioned her meeting her gaze.   
“Well, I cant wait, you made sure of that 22 years ago, let’s go missy!”   
“Ugh fine, don’t order without us!” Rory instructed the men and followed her mom. When she got in the toilets, she received a full ‘sassy hand on hip woman on a mission’ stare from Lorelai.   
“What’s this about?” Rory asked confused.   
“When were you gonna tell me about Jess?” Rory’s response gave it away instantly, yet she tried to hide it.   
“What about Jess?” She fidgeted around with her hands and avoided her gaze.   
“Well that’s confirmed it. Why can’t you tell me anything about your love life anymore Rory? You used to come to me for everything!” She looked hurt.   
“There’s not a lot to tell Mom, we love each other, that never stopped. Something happened at graduation, but we never got chance to talk about it until New York. We are never in the same place together for long enough to have a proper try with our relationship. Now I have this job, that could be the push we need. Paris and Lane got it out of me earlier, but I think Jess could be the one Mom. I’m ready to try and make this happen”. Rory looked up at her Mom shyly.   
“Yeah, nothing to tell Rory. Well, you sound like you know how you feel and you know what you want. Yeah, it wasn’t great when you were 16, but you’re 22 now and about to start your career. If you’re not ready now, when? I just think it’s a lot of change and having Jess will make your transition to New York much easier. I know you Rory, you never got your closure the first time around. This may be exactly what you need for this to work well this time around” Lorelai said softly.   
“Thanks Mom, having you on side with him this time around will make everything much easier” they shared a smile and she instinctively embraced her. “Also, we were going to tell you both together when we made sense of everything. Of course I want you in the know with my love life. You’re the love guru, my advisor and my best friend. Thank you Mom” Rory said genuinely.   
“Stop it or my make up will be wasted”. Lorelai laughed along with her daughter. “Come on, the boys will have eaten the menu at this rate!” She joked whilst holding out for her daughters hand which she gladly took. The pair walked back to the table to enjoy the rest of their evening.


	7. The Eve of the Times

The next two weeks absolutely flew by for the Gilmore Girls, it was the eve of her first day at her Times job, she was scrambling between boxes in her room of the house she shared with Jess, where she had officially moved in 4 days prior.   
“Jess!” Rory called out from between walls to grab his attention from the room opposite. “I can’t find my lucky outfit! Have you seen it?” she fretted around with a demanding sense of panic. By the time he made it into her room, he found her with her head fully submerged into one of the many giant cardboard boxes full of her clothes and books still scattered around her floor.   
“What lucky outfit?” Jess asked confused as he leaned against the door frames holding a tea towel and a wooden spoon. “Did you not label these boxes?” He teased pointing out the bold letters repeated clearly around the sides.   
“Clearly not bloody well enough!” Rory sighed loudly in frustration. Jess let out a soft sigh, headed over to where she was and pulled her out of the box and into his embrace.   
“Well, it’d be much easier if I knew what I was looking for, you’ve got many outfits here”. He said calmly, whilst he comfortingly rubbed his hands up and down her arms, helping Rory physically and mentally calm down.   
“Red dress, full skirt. I got it with my Mom the day after our meal in Hartford. I feel so confident in that outfit that I know I won’t need to try even harder to impress anyone tomorrow” she said.   
“Oh that one?” Jess almost laughed at her. “You must’ve forgot, but you asked me to hang that in my wardrobe when you had it shipped here straight from the shop you bought it from” the lightbulb went off immediately in Rory’s head and she leapt out of his arms and sprinted across the hall into his bedroom. When she located the garment, she squealed excitedly and grinned from ear to ear.   
“Thank you Jess, you’re amazing!” She reached up onto her tip toes to kiss him and attempted to continue onward to her room.   
“Ah-ah!” Jess blocked her exit and took the outfit off her, hanging it temporarily onto the curtain rail.   
“Jess! I need to make sure I am 100% ready for tomorrow” She exclaimed.   
“I have no doubt you will be Ror, but that will definitely be one of the only times I will ever get to see you sprint into my bedroom, I don’t intend on wasting this opportunity” he said huskily whilst snaking his arms around her and attacking her neck with his mouth. She giggled in response and used all her strength to push him onto the bed. Jess cocked an eyebrow as she seductively crawled atop of him and straddled his waist. She put all her weight onto her arms to pin him onto the bed, bent down and started kissing him from his collarbone, only pausing when she got to his ear.   
“Sorry, but I really need to prepare for this. We can continue this after dinner tomorrow” she then winked at him and used his shock period to dismount him and wander back into her bedroom with lucky outfit in hand.   
“You’ll pay for that Gilmore!” He shouted through to her and laid there for a few more minutes before heading in the shower. This caused Rory to laugh to herself as she busied herself making sure everything to the last detail was perfect for her first day at the Times tomorrow. 

Back in the Hollow, Luke hadn’t spent much time at the diner with helping both Jess and Rory settle into their new house in New York. He was absolutely thrilled when they told him they were going to give their relationship another try, he thought the world of the pair of them and always wanted what was best for the two most deserving kids, who he’d treated as his own anyway. The drive from Connecticut to New York hadn’t been too bad for them, but the lifting had certainly strained his back, maybe he wasn’t as young and fit as he used to be. As Luke reached over to grab Lorelai’s favourite mug so her coffee would be ready for her impending arrival, he felt his back ache and instinctively reached to grab at the muscle in attempt to relax the pain.   
“Luke honey, are you hurt?” Lorelai walked straight over to him with a very worried expression.   
“Hey, uh not hurt, I just ache from all that lifting” he admitted whilst passing her the fresh coffee mug he’d made for her.   
“Aw sweets, how about you let one of your guys close tonight and you can get some rest?” She cupped his cheek and gave him the look that he couldn’t resist. Luke sighed in defeat.   
“You’re right, I’m sure Ceaser won’t mind since Lane is opening tomorrow, I’ll go arrange it and then we can go, be right back” Luke said as he went into the back to locate Ceaser. Timed impeccably, her phone rang the minute he’d disappeared.   
“Hey Loinfruit, are you missing me that bad already? You wanted to talk to Mama?” She teased.   
“Well if you’re not gonna be a supportive listener, I can always ring Dad?” Rory sounded very stressed.   
“Wow okay, fire away crazy lady” Lorelai said with a hint of both sincerity and sarcasm, as only she could perfect.   
“I’m freaking out. It’s my first day tomorrow and as prepared as I am, I don’t think it’s enough. Jess has been great, but I need your help to calm my nerves” Rory admitted.   
“You do miss your mama!” Lorelai said happily. “Mama misses you too baby. Anyways, in regards to your preparation, read me your list aloud and we can check it together”. She suggested.   
“Thanks Mom” Rory sincerely said. “Okay, number one is lucky outfit”   
“Jess’s wardrobe, pressed and ready to go” Lorelai answered for her.   
“How did you remember that? I had a meltdown earlier as I forgot! Yes, Rory Gilmore forgot something she had deliberately planned ahead with to avoid this! I’m stressing out so much!” Rory let out a deep sigh and fell onto her bed.   
“Calm down hon, you have it now. It’s ready to put on tomorrow, no big deal. I presume the black Louboutin’s Grandma bought for you will match the dress perfectly!” She added.   
“I didn’t even consider shoes but you are so right! Thanks Mom, I’m so glad I called you”   
“Anytime sweets. So what’s number 2?” Lorelai asked her, as always knowing exactly how to calm Rory. The conversation continued for a few more minutes until Jess informed Rory he had dinner ready for them. After some teasing, they ended to conversation just in time for Luke to come from the back with his jacket and keys.   
“Sorry that took a while, I got a call from the bakery. Ready to go home?” He smiled at her.   
“Yeah, let’s go” she smiled back and followed him to the truck. 

The next morning, Rory awoke well before her alarm, her conscience not even giving her chance to open her eyes before she immediately felt an intense wave of nerves wash over her, quickly fighting to fill her eager mind with invading thoughts of panic and doubt. She tried to focus on the distant sunrise to distract herself from any negativity, awestruck at how it’s rays looked beating through the Venetians, illuminating her wooden floor into vibrant shades of oranges and yellows. She dragged herself to the shower in an attempt to calm herself, finding more comfort in watching the water flow down her body. 

The sound of running water had stirred Jess from his slumber. He squinted his eyes towards his alarm clock which read 5:19am, almost mocking him. After allowing himself a chance to come around he got up, threw on a shirt and headed over to the kitchen to make some fresh coffee. He knew how nervous Rory was to make a good impression today, so anyway he could try and compose her back to her calmer self, even if that means waking up at a silly time to make her coffee, he would do it.   
“Hey, why are you up so early?” Rory headed out of her room tying her dressing gown. “I didn’t wake you did I? Is that coffee ready?” He slid a fresh cup in front of her as she reached him which resulted in a half attempt at a cuddle and a kiss from her.   
“Good morning yourself, I woke up out of the blue and couldn’t fall back asleep. I heard you in the shower so decided to get up and put on coffee. Don’t worry, you didn’t wake me” he lied to her as she would feel guilty about it, knowing she didn’t need anymore stress today.   
“Oh, well that’s not good” she took a sip of her coffee. “This, however, is amazing. Thank you Jess”  
“Anytime Ror”. They sat around their centre island in comfortable silence reading whatever was closest to them.   
“You have just under 3 more hours until you need to be at the office, would you like to get everything ready and go for breakfast?” Jess offered, she nodded firmly in response with a small smile. “That would be lovely, although I’ll probably take a while getting ready. My stomach is in shreds. I mean, what if I get it wrong? Maybe they won’t like me and decide that I wasn’t worth their time”  
“Hey! The nerves are speaking for you again. You know you’ll do great Gilmore” Jess closed the distance between the two and wrapped his body protectively around hers from behind her. She felt an instant calming sensation slither through her body and melted into his embrace.   
“I wish you could come with me and keep me calm, you always know what to say” she tilted her face and pressed a kiss to his bicep.   
“Maybe I can’t, but I can treat you to breakfast before to get you going” he kissed her neck causing her to giggle. “Now go! Get yourself ready and I’ll be right here for you when you’re ready” he spun the chair and lifted her of the seat. She allowed him to put her down, give him a quick kiss and wandered off into her bedroom. 

They decided they would have separate rooms in this place as they didn’t want to rush into anything too serious between them yet. That being said, out of the 4 days she had now lived there, she had only spent the night previous alone. Rory sat on the bed and began to comb through her wet hair. She allowed her mind to wander back to a year ago and recollected how she had been in sort of a similar situation. Living in a fancy apartment belonging to Logan, she thought her life was perfect with him and that they would be together for as long as she lived. Remembering all the pain and belittlement he had brought to her was almost unbearable to think about, even now being in a loving, although complicated, relationship with Jess and starting her dream job, Rory would never forget how she was made to feel as those scars ran far too deep to heal. She hadn’t even dreamed of ever comparing Jess to Logan, they shared a much deeper, special kind of love and he really knew and understood her. He took the time to get to know her instead of showering her with expensive gifts for affection. She understood why things happened how they did when they were seventeen, and she didn’t hold anything against him for it anymore. The bond shared between the two of them was unbreakable, the love there was beyond compare. She was absolutely terrified of the thought of anything bad happening in their relationship, but how could she ever hope to understand what being truly loved felt like if she didn’t take the risks? Rory shook her head snapping herself out of her thoughts and flashbacks, she had to focus on mentally preparing herself for today. She clipped up her hair, put on her lucky outfit and picked up her briefcase. After a quick touch up at the mirror and a read through of her mental list, she walked out of the bedroom. She found Jess lazily typing at his laptop, he had showered and changed in the time she had taken to get ready and decided to start editing early.   
“Hey, how do I look?” Rory twirled for him.   
“Very nice Gilmore, but I must say you ask for a biased opinion since I would find you beautiful in nothing but a bin liner” he closed his laptop shut, walked over to her and wrapped his arms around her.   
“You look great, you’re going to be absolutely flawless today. I am so proud of you” she smiled softly as she fell into an embrace. He broke them apart with a kiss and grabbed his wallet and keys.   
“Ready?” He asked her. Rory took a deep breath and nodded, they exited the house together and walked harmoniously in step with one another arm in arm down the sidewalk towards their favourite café.


	8. Surprise?!

By the end of her first week, Rory was thrilled with the progress she was making within her role. She had submitted her first piece already and had made some great friends within her department. As the clock hit 5pm in the quiet of her office blocks, she grabbed her coat from over the back of her chair and departed for the weekend. When she got to the exit, she saw Jess leaning against his car with a smirk plastered onto his face. 

“Hey, what are you doing here?” Rory practically skipped across the sidewalk to get to him, threw her arms around his neck and kissed him gently.  
“Hey yourself. I’m taking you away somewhere, it’s a surprise so I’m not telling you anything, but you may need these” Jess said mysteriously whilst handing her some yellow ear plugs.  
“Ear plugs?” Rory questioned confused. “I didn’t realise the Distillers were touring?”  
“Well they probably would be had they not broke up in 2006” he answered sarcastically. “Come on, hop in. I got you some clothes in the back for you to change into when we get there”. He then got into the car without another word.  
“Wait.. what?!” Rory got into the passenger side whilst firing questions at him about the trip. Jess hushed her with a kiss, put the Sex Pistols on his stereo and drove off. 

After getting nowhere with her interrogating, Rory finally gave up asking where they were going and stayed silent. An hour or so later, Jess turned off the highway to make a coffee stop. Rory immediately recognised the service station, realising that they were heading towards Stars Hollow. She didn’t let him know that she had worked out where he was taking her, she had accepted that Jess had organised this and would not pry any further. Rory knew full well she would enjoy whatever surprise he had prepared for her. When they pulled up, Jess went in to go and buy them both a coffee and Rory used the opportunity to change in the restroom. He had packed her a dark green dress and black heels, which caused her to again wonder what exactly they would be doing once they got there. By the time she was ready, Jess was already in the car with a smile on his face and had an XL coffee for her. He told her she looked beautiful, gave her kiss and without another word, started the ignition. Around 20 minutes later, they pulled up outside Luke’s. 

“What are we doing here?” Rory questioned him.  
“Just putting our bags upstairs. I’ll sort these if you want to get yourself another coffee”. He answered her vaguely and busied himself whilst Rory practically skipped around the counter to fill a takeout mug. She had finished her coffee by the time he had got back to her, she swore she had heard him on the phone as he descended the stairs.  
“Right, let’s go!” Jess said, taking her hand into his and leading her out the diner.  
“I’m really confused, where are we going?” She asked rather impatiently.  
“Relax will ya!” Jess laughed. “You trust me right?” Rory nodded in response.  
“Then shut up for a minute and let me surprise you!!” He quickened the pace slightly and headed towards Miss Patty’s. As they got closer, she could hear the faint music playing become louder. Much louder.  
“I’m guessing this is what the plugs are for?” Rory said using her free hand to dig through her jacket pocket to locate the pair Jess had presented her with earlier.  
“Something like that. Why don’t you pop them in, don’t want to deafen you” Jess answered. When she put them in, he slid open the door to a..  
“SURPRISEEE!” Practically everyone in town was present stood under a huge hand painted ‘Congratulations on your Dream job Rory’ banner, most probably by Luke. She immediately ran to him and Lorelai who both had proud looks plastered onto their faces. The band had stopped playing the second Rory had opened the door, as Lane got straight up from her drum set and went over to her best friend.  
“Rory hey!” she wrapped Rory in a very tight hug. “Do you like your surprise?”  
“It’s wonderful!” Rory answered truthfully. “I’m really overwhelmed!”  
“Well, we’re all just so damn proud of you!!” Lane answered. “Plus with everything happening so fast, we never got to throw you a ‘Good Luck and Good Bue’ party” Lane added.  
“Yeah and you know us town folk love a good party!” Loreali added throwing her arm around her daughter.  
“It’s amax! You all didn’t need to go to this much trouble for me though! I don’t need a party” Rory said.  
“Don’t thank us sweets, it was all Jess’ idea!” Lorelai replied. Rory looked around the studio to find him, catching him talking with Luke. She found herself speechless that Jess, her Jess that absolutely despised Stars Hollow and the vast majority of its inhabitants, would go to all this effort for her. Then again, he had done a full one-eighty from 7 years ago when he first arrived and she knew that he truly loved her and would do anything to make her happy.  
Rory excused herself from the ladies and approached Jess, asking him to take a walk with her. Many people were bugging her for leaving the party so soon, but she promised everyone she passed on the way out, especially Babette, that she would only take a few minutes and be right back to properly celebrate her first week at her dream job. 

“Where are we going?” Jess asked Rory as he allowed her to lead him down the steps of Miss Patty’s studio.  
“The lake, but not for long though” she replied.  
“Okay..” Jess was confused but followed her nonetheless. When they arrived, she motioned for him to sit across from her, similarly to how they did many moons ago at the bid-a-basket festival.  
“This reminds me of our first date” Jess reminisced.  
“You call out-bidding my ex-boyfriend to get a rise out of him a date?” Rory laughed.  
“Anything to spend time with you Ror” Jess smiled.  
“Yeah, and to piss Dean off” she retorted.  
“Ah, all part of the fun. Such an added bonus” he laughed. “Anyway, why are we here?” He asked her.  
“Jess..” she took his hands in hers before continuing. “I just wanted to thank you for all this, and well, for everything you’ve done for me” blue met brown as she spoke. “I don’t think I could have achieved any of this without you. Graduating Yale, moving to New York, working at the Times, all of it!” She said genuinely.  
“Ror, you know that’s not true. Of course you would have done it without me, I helped you get back on the right tracks now and then sure, but you did the hard part. I was just here for the ride” he smiled.  
“Dirty!” Rory giggled.  
“Yeah, but it’s true though” he winked.  
“God Jess! Mind out of the gutter please, I’m trying to be sincere!” She laughed.  
“Then please, continue” he smiled.  
“Thank you! I just wanted to say that you’re incredible and your support means the world to me. So, thank you” she said very meaningfully.  
“Well, what kind of boyfriend would I be if I didn’t support you?” He added.  
“Boyfriend?” Rory asked fast.  
“Aren’t we? I mean, we live together and sleep together” he smirked.  
“Well, I don’t recall being asked Mariano” she retorted.  
“Well, in that case. Rory Gilmore, will you be my girlfriend?” He asked her lovingly. She gently put her hand on his cheek and leaned into a passionate kiss.  
“Does that answer your question?” She giggled.  
“I’m not sure, wanna try again?” He smirked.  
“Sure boyfriend” she leaned back into kiss him and smiled widely.  
“Well now that’s all sorted, do you want to head back to your party?” He stood and pulled her up with him.  
“Let’s go” Rory smiled at him and leaned into his shoulder. 

It was at this moment that she knew that everything was going to be just fine. That all the hard times were behind her now. She had her career, she had her home, she had her family and she had her Jess.

**Notes for the Chapter:**

> I’ve decided to wrap this up due to bereavement. Thank you all for reading, I hope you enjoyed this story as much as I enjoyed writing it! 
> 
> Much love,  
> YorkshireRose18


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